Most people think success comes down to talent, timing, or even luck. But Kyle Austin Young suggests it could be a numbers game. In this episode, he explains how to think about success through the lens of probability so you can actively improve your odds over time.

JR and Kyle explore:

• Why your goals have hidden probabilities attached to them
• How to reduce the likelihood of failure
• The power of repeated attempts
• When to power through to achieve your goals, and when to pause
• Why differentiation is critical in today’s market

This conversation reframes success as something you can engineer. Whether you’re early in your career or reevaluating your next move, this will help you make smarter decisions and create better outcomes over time.

Tune in every week for more episodes like this. Subscribe on YouTube and follow Career Sessions wherever you’re listening to this.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/kyle-austin-young

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How Successful People Actually Think About Risk, Failure, And Opportunity, With Kyle Austin Young

Most people think that success is about talent and timing, maybe even luck, but what if that’s not the complete picture? What if success is less about being extraordinary and more about playing the odds better than everyone else is doing? My guest, Kyle Austin Young, has built his work around this deceptively simple idea, which is that success is a numbers game, not in a shallow hustle way, but in a deeply strategic sense.

How do you take more shots, yes, but more importantly, how do you take better shots? How do you position yourself so that, over time, the math starts to stack up in your favor? Kyle is a contributor to Harvard Business Review and Forbes and Fast Company and Psychology Today, and his perspectives aren’t just theoretical. He’s lived through setbacks, he’s been laid off a couple of times, and he’s used those experiences as a way to rethink the realities of his career journeys.

In our conversation, we’re going to unpack the hidden math behind success, what people get wrong about it, and what they get wrong about resilience, and how to tilt the odds in your favor, whether you’re early in your career or rethinking your next move because success is really a numbers game. The question is, how well are you playing it? Kyle, welcome and thanks for joining me.

Thank you for having me. I’m excited to be here.

Fundamental Misunderstanding About Success As A Numbers Game

Yeah, absolutely. Let’s jump right in and talk about your book. The title is simple and yet provocative. What do people fundamentally misunderstand about success being a numbers game?

There are a few things we misunderstand, but I think at the basis a lot of people don’t realize that every goal that they’re pursuing has two hidden numbers attached to it. Their odds of success and odds of failure. I think one of the reasons why we spend so little time thinking about that is we assume that our odds are unknowable, unchanging, and therefore irrelevant.

I wrote this book to help people realize that there are ways that we can actually wrap our minds around our current odds of success. If we do that, we can then actually improve our odds of success. In the context of a single goal, that can change your outcome, but over the context of many goals, that can change your life. I think the fundamental misunderstanding just starts with recognizing that this is even possible.

Obviously, all of this is about probabilities. As you say, probabilities of success and probabilities of failure. What are some of the variables that people should be trying to influence?

The Counterintuitive Strategy Of Thinking Negative And Probability Hacking

Well, what I find to be one of the most straightforward ways to improve our odds of success is to do something that’s a little counter-intuitive. I’ve found that when most people are pursuing a big goal, the advice they’re usually given is to think positive, don’t worry about what could go wrong, that’ll just discourage you. If it’s meant to happen, it’ll happen. Just pursue your goals with gusto, and that’s the most reliable way to succeed. I encourage people to do the exact opposite. I literally encourage people to think negative.

That’s a big part of the probability hacking process, because we can understand probability a little bit like we’ve traditionally understood matter. This idea that matter can’t be created or destroyed, but it can be transferred and rearranged. The odds that we want are currently hiding in our potential bad outcomes. If we think about a game where we’re flipping a coin, if it lands on heads we win, tails we lose. There’s a 50% chance we’ll win and there’s a 50% chance we’ll lose because it might land on tails.

Now, I don’t know how to influence a coin toss, but in real life, there’s typically things we can do about the bad outcomes that are hogging some of the probability we want. As we make those risks less likely to materialize, we boost our odds of getting what we’re actually looking for. My framework is ultimately designed to help people identify what are the potential bad outcomes, how can we use our creativity to take some of those risks off the table. If we do that intentionally over the course of the goal, I give people ways to break it down into a diagram, and if we do it step by step, we can end up with dramatically better chances of getting what we want.

What are some of the specific ways that you can reduce the odds of a bad outcome so that something becomes more of a good bet?

Practical Application Of Reducing Bad Outcomes (First Job Example)

Yeah, if you’re open to it, let me do this in the context of an example. This won’t have any numbers in it. I tell the story in the book. It’s the story of how I got my first job out of college. This was many years ago. I’d just graduated with this undergraduate degree and I wasn’t really inspired at all by the opportunities that I was seeing. I decided to do something really audacious.

I decided I was going to apply to become the product development director at a health organization. I’m 21 years old. If I get this job, I’m managing people in their 50s, 60s, 70s, people who could have been my grandparents at the time. I decided to apply for this job, and I got the interview, and so I had a real chance. Even at this point in my career, I wanted to ask the question. “What can I do to improve my odds of success?”

This was before I was a consultant, before I wrote this book, before I did any of this stuff. I said, “Let’s see what we can do,” and so I tried to identify what are the bad outcomes that might happen instead of the outcome I wanted. At this point, all I needed was a job offer. I already had the interview, so there was just one step left. I identified three risks, three big threats to my success.

The first was that the hiring squad might take one look at me and just think, “He’s too young. There’s no way somebody this young can manage the department.” I needed a way to try to minimize that risk. A lot of people would say, “Well, there’s nothing you can do about that. You know, you could lie and say you’re older than you are.” I wasn’t going to do that. “You could, I don’t know, wear a paper bag over your head.”

A lot of people look at an obstacle like that and say there’s nothing you can do with it. I found something I could do, which is I grew a beard. That simple change to my appearance made me look a good bit older than when I didn’t have the beard. It took some of the edge off when I walked into the room. It wasn’t like “Who’s this kid? Where did he come from?” It looked like maybe I could pass for somebody a little bit older than I was.

Another risk that I identified was they might be concerned about my lack of experience, which was real. I had just graduated from college and I was up against candidates who had a few decades on me in terms of their work experience and all of the things that they’d done over that time. Again, I wasn’t going to lie, but I did want to ask myself the question, “What can I do to take some of the risk out of that?”

“What can I do to maybe reframe the conversation so that it’s not just a conversation about how I don’t have any experience?” I actually typed up a plan for how I was going to turn this product development team around, and it was so thick I had to have it spiral bound. It was a book. I took it in with me, a bunch of copies, and I handed it out to every person I interviewed with.

When they would ask questions about my resume, I would just redirect it to be a conversation about my vision for the future of the department. They’d say, “Tell me about a time you overcame adversity,” and I’d say, “Well, let me tell you how I’m going to overcome adversity as it relates to this thing that the product development team is dealing with.” that was a way that I de-amplified some of that risk.

The third and final threat that I perceived was the thought they might be concerned I just couldn’t get along with the existing team because of the generational gap. “Is he going to be able to fit in with this group of people?” I did something that I’ve continued to use since then a really great strategy. I asked if the team had read any books lately as a group.

They said a few titles, and I went out and read every single one. What that did is when I was then in these interviews, I could speak their language. I knew their jargon, I knew the frameworks that they were referencing, I understood their goals better. I found myself in a group interview at one point. It was me and some of these other candidates. They were all much more experienced than I was.

One of the books the team had read was called The Whuffie Factor. Not a lot of people are still reading The Whuffie Factor, I don’t think, but it was a book about how brands generate social capital. Somebody presented an idea and I said, “You know, I think that’s the idea that could get us a lot of Whuffie.” I remember looking around and the other candidates, their eyes are bugging out of their head. “What on earth did this kid just say? What is Whuffie? What’s he doing?”

I looked at the existing team members, and they’re laughing. They knew exactly what I was talking about. They just read that book. When it was all said and done, I got that job. At 21 years old, I became the product development director at this health organization and it completely changed the trajectory of my career. I would later encounter a couple of layoffs and that led to the consulting.

That was just such a massive leap forward for me. What made that possible was thinking negative. What made that possible was recognizing that the odds that I wanted were hiding in my bad outcomes. Those were the things that could have happened instead of what I wanted. I did everything I could to take those things off the table and ultimately got what I was after, which was a really unlikely opportunity.

I hear two things in what you said. One is you were directly confronting the negatives. Objections that people were going to have. Anybody who’s in this sales process will certainly say that that’s a key thing that you often have to do to make a sale. You were trying to convince them to hire you, so it is a form of a sale. Any process where you’re trying to influence somebody or sell somebody, being ready to confront the objections is a key thing. I think that’s one thing you certainly did.

I think the bigger thing listening to what you’re saying is you stacked the odds in your favor by going the extra mile. Coming in with a playbook. Most people think, “I’ll do that after I get the job.” You did it before you got the job. As somebody who’s hired a lot of people in my life, having somebody who’s come in and actually thought about it, that makes a huge impression because you’re saying, “I’ve already thought about this and I’m deeply committed to the success of this and I haven’t even gotten the job yet.”

To me, that just stands out a ton. It’s part of what you’re saying, which is you’re both reducing the odds of a bad outcome, but you’re also pushing some things onto the likelihood of a good outcome. You’re managing both halves of that coin flip, if you want to go back to your analogy of the coin flip from a few minutes ago.

I think that’s absolutely true. I think what’s key about this framework is I know there’s a lot of people out there who want to go the extra mile. They want to work hard, they want to do everything they can to succeed, but they aren’t necessarily sure where they should be investing their time. I encourage people to create what I call a success diagram. It’s just a list, left to right, like a map of, “Here’s everything that’s going to have to go right in order for me to get what I want.”

For each thing that we need to go right, beneath it I then make a list of the things that could go wrong. “What are the potential bad outcomes that could happen instead of what I want?” when we have that out in front of us, it gives us a really powerful opportunity to take a bird’s-eye view and ask the question, “What can I do about these bad outcomes? In what areas can I go above and beyond?”

Otherwise, we all know that person who’s working really hard, maybe they’re not getting the results that they want. Sometimes we feel like we are those people. That’s because to some extent, it’s not really about how hard we’re working, it’s about are we working hard on the right things? I find that whenever everything’s done in the context of what has to go right in order for you to get what you’re looking for and what could go wrong, we make sure that we see a good return for the efforts that we’re putting in.

A lot of people seem to want certainty before they act. How do you get them comfortable with operating without it?

The Power And Limits Of Multiple Attempts To Achieve Unlikely Success

I think I start by just making it clear that you are operating without it whether you like it or not. I’m sorry to bust the illusion of certainty, but you never had it. Also, in the book I talk about the power of multiple attempts. I had the opportunity to interview somebody who played on the 1980 US men’s Olympic hockey team, the “Miracle on Ice.”

I show, using numbers, how this was called this miraculous thing that the United States beat the Soviet Union when they were so outmatched. As an individual event, it was. If you look at the fact that they played 9 times total, the US won 2, the Soviets won 7. That’s not a miracle. Going 2 and 7 in a 9-game rivalry, that’s not a crazy outcome at all that you would win 2 out of nine games. That’s just a difference in ability, a difference in skill.

I try to illustrate for people that through the power of multiple attempts, we can accomplish things that seem unlikely. I think that’s something that takes a little bit of the edge off when it comes to failures when you recognize that almost all of the big success stories that we’ve seen in history, or maybe not all, but many of them incorporate this element of repeated attempts.

We think about the arts, and we think that the most successful artists are the ones who are the most talented. We realize that Mozart, who maybe we know 5, 10 pieces of music that he composed, he composed over 600 pieces of music. We think of these people as being incredibly talented, and they are, but there’s also a component in this that they just tried over and over and over and gave themselves so many opportunities to find success.

One more story I tell in that same vein. Thomas Edison. When he’s trying to invent the incandescent lamp, it all comes down to finding a practical filament. He needs something that can get hot enough to glow without catching on fire or snuffing out so quickly that there’s no point in even trying to have one of these in your home. He’s up against a number of other inventors who are trying to do the exact same thing.

It wasn’t that he had an idea no one else had thought of. It wasn’t necessarily that he was even significantly more talented than they were. What he did that they didn’t do is he experimented with 6,000 different filaments to find 1 that worked the best. He actually found that carbonized bamboo, which is probably not the first thing you’re going to try, that was the one that incandesced the longest without catching on fire.

He ends up being awarded these valuable patents that change the trajectory of his career. Through repeated attempts, we can find unlikely success. What we need to realize is once we have that success, it changes our odds in a long list of subsequent goals. Even if we succeed through this inglorious process of trying over and over again, that doesn’t change the fact that once we have the success, we have the ability to then go chase bigger goals with much better odds.

You hear these stories. Van Gogh was famous for just taking a brute force approach, like, “I’m going to learn to be a great painter if it takes me my entire life,” and he just painted and painted. Edison, I think famously said something to the effect of, “I haven’t failed a thousand times” or whatever the exact expression that he used to describe the fact that it took him a long time to get to where he ultimately got with trying to invent a workable light bulb solution. How do you know when you’re trying to brute force your way through this and just giving yourself a lot of attempts? When does that persistence become irrational? How do you know when the odds just aren’t worth playing anymore?

One way that we can get a sense of our odds of success is to create a success diagram but then put some numbers on it. Ultimately, we can understand our odds of accomplishing a goal as the odds of each individual thing that has to go right multiplied together. I’ll give a really simple example of that. Let’s say that you’re training to run a marathon. I just ran my first half-marathon.

You hire a running coach and she says, “I can get you ready by race day, but there’s three things you’re going to have to do. I need you to eat, sleep, and train according to the regimens I’m going to create for you. If you stick to all three of those things, you’ll be ready, but if you don’t, if you cheat on even one of them, I’m not going to be able to get you ready to run such a big distance in a short amount of time.”

If I’m going to create a success diagram for that, there’s three things that have to go right. I need to eat, sleep, and train according to these parameters, and if I do those things, then I’m virtually guaranteed success according to this running coach. Let’s just put some really easy numbers on that. Let’s just say we think it’s 70% across the board. 70% chance I’ll eat the way I’m supposed to, 70% chance I’ll sleep the way I’m supposed to, 70% chance I’ll train the way I’m supposed to.

This is where a lot of people fall into a trap called averaging. We assume that if we feel good about our individual steps to accomplish a goal, we can feel good about our odds of the goal in its entirety. That’s not true. In reality, we can’t average these numbers, we have to multiply them. What’s really surprising to a lot of people is if you multiply that out, .7 times .7 times .7, you learn that you only have a 34% chance of accomplishing this goal.

At first, it seems like such a slam dunk, but it’s actually not. This is a predicted failure. You might succeed, but we don’t expect you to succeed. We expect you to make a mistake in one of these three areas and ultimately not be ready on race day. We have an opportunity to get some sense of our odds of success when we break it down into its component parts and try to make some estimates of how likely are each of the things that I’m going to need, how likely are those to ultimately come to fruition.

There are some other rules that can help us estimate. You know, we’re not going to have all the information, but we can know that our odds will never be higher than the odds of our most improbable prerequisite. If there is one thing that has to happen, has to happen in order for you to succeed, and it’s incredibly unlikely, then your overall odds are going to be even lower than that because it’s not the only thing that has to go right.

We can start to get a little bit of a sense of, “Is this a 1-in-10 type of goal? Is this a 1-in-100 type of goal? Is this a 1-in-1,000 type of goal?” In some cases, if you’re Thomas Edison looking for a practical filament, it’s okay if it’s a 1-in-6,000 type of goal because it’s not that hard necessarily to just experiment with these different filaments. You’ve got a timer, it’ll tell you which one works the best.

Is it practical, though, to start 1,000 businesses and hope that one of them is successful? Probably not. That’s probably not a practical goal. You’re absolutely right that we want to get a sense of what this number is in our lives. We can’t necessarily do it exactly, but when we break it down into its component parts, we find that we can get a pretty good estimate and at least know to some extent what the limit of our opportunity is. “Here’s best-case scenario.”

There are times where that tells us that maybe this isn’t a goal to prioritize right now. Ask yourself the question, “Which one of these should I be going after right now?” a lot of times when we order our goals by how likely we think they are to happen and prioritize the ones where we have a real shot, we can then improve our odds at some of those things that might currently seem more far-fetched.

How did you come to all of this? How did you put together this philosophy? Obviously, there’s a lot of statistics and math involved in it, but how did this become core to the way that you think about success and failure?

I think a lot of people’s origin stories, it wasn’t the story that I designed for myself. When I got that job as product development director, I thought that I’d set myself up for a pretty fantastic career. For the first few years I had. I had a lot of success. Ultimately there was a round of layoffs that I was included in. I moved across the country for another job. There was a round of layoffs that I was included in.

By the end of it, I’d had two pretty visible, pretty respected leadership positions and all I had to show for it were two layoffs. The first time, my wife and I just bought our first home, that wasn’t ideal. The second time, we were in the process of adopting our daughter, which is a pretty famously expensive process, and so twice I had to sit down my wife and say, “I lost my income.”

At that point, I didn’t want to just stay on what felt like this hamster wheel of, “Get another great job, lose it. Get another great job, lose it.” I had some friends who were really generous with me. It was pretty well known after the second layoff that I had four job offers the next day. People knew that I was still in demand and that was really helpful.

Some people reached out to me and said, “I’ve heard that you’re trying to decide which one of these four jobs to take. What if you took a fractional role with each of the organizations, positioned it as consulting, and then put yourself in a position where you’d have a more diversified income?” that was over a decade ago, but I took that advice. One of the biggest things I carried with me into that consulting career was I learned through the layoffs that it wasn’t just a question of my personal performance when it came to my job security.

It was possible to do a really good job, get great performance reviews, and then still find myself without an income very suddenly. Ultimately, what I realized was if I wanted to do everything I could to stay gainfully employed, it wasn’t just about what I was doing. It was also about whether the projects I was involved in were succeeding or failing, even if that meant going outside of maybe the scope of my job description.

“What could I do to make the project successful, to make sure the company had money, to make sure that I was in a position where I could still be okay?” that’s what led to this idea of when I would enter into a new consulting project, I would make a diagram where I’d list out everything that had to go right in order for the project to be successful.

Sometimes that just meant asking the right questions. “Have we thought about this? What are we doing about this risk over here?” I wanted to take a higher level of responsibility and put myself in a position where I was doing everything I could to make the team succeed, realizing that that was going to be the thing that ultimately kept me employed.

Ten years down the road, how does this impact how you think about the trade-off that somebody might be considering between having one full-time job versus the path that you’ve chosen, which is to have multiple income streams and different consulting projects? How do you think about that trade-off?

It’ll be different for different people. I can tell you my story. In my life, I now probably make maybe six or seven times as much as I did when I was a product development director, so there’s no cap on your income, there’s an opportunity for tremendous growth in that vein. There is some diversification, which is really nice. You will go through the experience of losing clients more in this model because you have several clients.

You’ll get laid off more often, so to speak. However, you have this diversification, so when it happens, it’s not as big of a deal, and that’s something that’s been helpful for me too. Financially been very rewarding for me. I can’t guarantee that everybody would have that same success. I’ll also say that a con that I do experience is you have 6 or 7 retainers at any given time, there’s always going to be a client who’s having a great day and there’s always going to be a client who’s having a terrible day.

If you want to go on vacation, you can do everything you can to minimize the risk of something catching on fire while you’re gone, but you’ve got maybe 7, 8, 9, 10 different organizations that need nothing to catch on fire for a week, and so in that sense, the odds work against you. You’re always on a little bit. I enjoy what I do. It’s unique every day, lots of different experiences. I get to learn from a lot of different people, so it makes me better at what I do. It’s been a great fit for me. I think ultimately, people are going to have to answer that question for themselves because there is some work to get to where I’m at, and you need to decide if that’s an investment you want to make.

Using Setbacks For Intentional Self-Reflection And Reinvention

Coming back, you had some setback moments. You talked about the couple of layoffs. When somebody has a setback moment like that, what advice would you give them to try to regain a sense of control?

What I have found every time I’ve been laid off, and I really mean this, is it has always helped me reinvent in a way that’s been really positive. It’s just an unexpected call to self-reflection of, “Okay, I designed a life that isn’t going to go the way I thought. Now let’s pause and ask the question. ‘Is there anything I wish was different?’ because we’re going to have to find a new job anyway.”

Success Thinking: Every time I’ve been laid off, it’s pushed me to reinvent myself in a positive way. It’s really an unexpected invitation to self-reflection.

In some ways, I think it can be a really helpful thing for people to have those types of setbacks because it forces us to think more intentionally, which we can do without the setback. You can be gainfully employed and stop and ask the question, “Is this the job I want? Is this aligned with my values? Is this putting me on the path that I want to be on?” I find that I tend to just get caught up in the day-to-day.

I’m on my to-do list, I’m in the entrepreneurial sense, working in the business, not on the business or in my life, not on my life. It puts us in a position when we’re laid off where we have to pause and ask that question. For me, I live in Nashville, Tennessee, which I’m very thankful for because of a layoff. That’s the reason that I ultimately moved here. I don’t know if I would have made that move otherwise.

I think it’s been a really good move for my family. I think I would have just kept working in that job that I started with. Whether you’re encountering a setback or not, I would encourage you to pause and ask those big questions of, “Is how you spent yesterday the way you want to spend your life? If not, then maybe there’s an opportunity for change,” and I don’t know if that’s ever more apparent than when we’ve been laid off because it takes away that fear of losing what we have. We already lost what we have. We’re on the other side of that fear. Now it’s just a question of what do we want?

One of the things you talk about speaking of pausing is pausing goals. What do you mean by that and what’s the advantage in it?

There’s been a little bit of a movement lately telling people to quit their goals or if they have too many goals, quit goals. I think that’s nonsense. I don’t know why you would ever need to quit a goal. Just pause it. Just say, “I’m not actively pursuing this goal right now,” but that doesn’t mean you won’t ever pursue that goal. I wanted to write a book since I was like eleven. That’s a goal that I’ve had for decades and decades.

It wasn’t even close to realistic at that time. It wasn’t close to realistic when I was a product development director or when I was an operations manager. It became realistic when after a decade of consulting and writing for Harvard Business Review and Forbes and Psychology Today, people were coming to me saying, “How do you think about this? Teach us the framework that you’re using because we’re seeing results from you that we’re not seeing from other people.”

That’s when I finally had the opportunity to write the book. I’m not as big a fan of quitting. I’m a bigger fan of pausing. I think you can do it really intentionally, and it’s in this same context of a success diagram. For the goal that you’re pausing, write down everything you can think of that will have to go right for you to accomplish that goal, start thinking of some of the things that could go wrong.

Just hang on to that sheet of paper. Keep it nearby. What that allows you to do is then live your life and you can passively collect the advantages you’ll need to one day pursue that goal. In the same thing of the context of me writing that book, I had an opportunity at one point to take on a project that wasn’t going to pay very well, but it was going to put me in close contact with a number of literary agents.

I knew what my goal was. I said, “Yeah, I would like to do that.” Why? I knew that someday I wanted to write a book, and I knew that one of the things required in order to achieve that goal was I was going to need to have a relationship with some literary agents. When that opportunity came up, I took it. We have an opportunity to pursue goals like that where it’s not necessarily the thing that’s at the top of our to-do list, it’s not on the front burner so to speak. However, as we’re going through life, we have an opportunity to meet people, connect with people, and gather up some of the advantages that we’ll need to one day move that goal back to the active list instead of the “someday” list. That’s why I believe in pausing.

You’re going to fail, right, along this journey. When you fail, how do you make sure that you get as much value out of that as possible?

Repurposing Assets From Failed Goals For New Outcomes

For me, it goes back to the success diagram. It goes back to looking at what steps have already been accomplished in pursuit of this goal because then we can ask the question, “How could we maybe reposition some of the assets we’ve accumulated in pursuit of something different?” In the book, I tell the story of these friends who I believe were former paypal employees, and they decided that they were going to start an online dating site together.

This was at a time when the internet was much newer, and they wanted to differentiate themselves by giving people the ability to upload a video just introducing themselves to other people who might want to maybe go on a date with them. That was cutting-edge technology at the time that they were doing this. They’re trying to get people to use the service, give it a try.

They’re running advertisements, they’re paying people money just to create an account, just upload a video and say, “Hey, I’m Kyle, here’s a little bit about me, here’s what I’m looking for,” and they just couldn’t do it. They couldn’t get enough people to start using the service to ultimately then go out and run advertisements and say we have all of these people looking to find love. Finally, they decided that they were going to not necessarily quit the goal, but repurpose it.

They were going to try to take what they’d already accomplished and use it toward a different outcome. The biggest thing they’d accomplished was they’d given people the ability to upload videos to the internet and anyone could do it. You didn’t have to be a programmer, you didn’t have to be a computer scientist, you could record a video, put it on the internet. That was crazy.

Instead of using it in the context of a dating website, they decided to broaden their scope and let anybody upload videos to the internet. Ultimately, they called it youtube. It was a failed goal, so to speak, that was incredibly lucrative, incredibly successful by many standards because they stopped and they didn’t run away from it. A lot of us run from failure.

Something goes poorly, “I don’t want to think about that, that’s embarrassing. I don’t want to be associated with that.” Instead, they recognized that there were a lot of smaller accomplishments that had happened in pursuit of that failure. Those accomplishments were still valuable. They could still be used in other places. Ultimately, they just took what they’d built, pointed it toward a different outcome, and were able to achieve enormous success.

I think a lot of us have left tremendous value behind when we try to distance ourselves from our failures. I encourage people to use that success diagram to remind them of, “Here’s all the things we’ve learned, here’s all of the assets we’ve accumulated. Is there something different we could do with these advantages that we’ve worked so hard to get?”

Avoiding Sameness Through Strategic Differentiation And Credibility

I know you write a lot about standing out as well. Why do so many people in business seem to default to sameness?

I think one of the biggest reasons. The people who are responsible for differentiation or at least image are often incentivized in a way that’s out of alignment with what might be the company’s best interest. If you think about like an established organization, if you’re an employee who’s responsible for that brand’s image, do you want to be the person who walks into your boss’s office and says, “Boss, I took a big risk today, but it might pay off for us?”

Most people don’t want to do that. That’s a weird conversation to have. To some extent, that is the price of being a little bit of a renegade when it comes to your branding. You have to be able to stand up to your superiors and say, “I’m taking risks. I’m doing things that might go really well or might not.” in reality, I think a lot of the employees in those roles find themselves in positions where it might be smarter for them to just play it safe and say “I’m following best practices,” and then if something goes poorly, they can blame it on the economy or blame it on some market force versus it all coming back and saying, “Maybe you shouldn’t have taken that big risk.”

I think that what’s important is, again, if we know exactly what we want, we know what it’s going to take to get it, we know what could go right, we know what could go wrong, we can take a lot of the risk out of a rebrand. We can take a lot of the risk out of being different and make sure that, just like we weren’t wanting to work hard for the sake of working hard, we aren’t trying to be different for the sake of being different. We’re being different in the areas where we need to be different.

How would you suggest that people practically speaking can differentiate themselves, particularly if they’re early in their career?

It depends to some extent on the industry that you’re in, but to some extent, I would encourage you to go back and ask the question, “What is the problem I’m trying to solve for my customers? How are other people solving it? What are just the biggest remaining frustrations that people have? What are they still mad about?” Are they mad that they don’t get enough one-on-one support? Are they mad about the prices they’re paying? Are they mad that there’s certain features that don’t exist?

That’s your biggest opportunity for differentiation. It’s not just, “How do I be different?” It’s, “How do I be different in the context of my customers’ goals?” when you recognize that, it can put you in a really powerful position. If you don’t have access to that information, you aren’t sure what to do, then I would just tell you to default to incredible customer service. If you are just killing it from a customer service standpoint, then in my experience, you’re going to automatically beat out so many of your competitors.

Also, put yourself in a position where some of that innovation will happen because if you’re taking your customers’ concerns really seriously, it’s going to lead to improvements in your product suite. I find that when you demonstrate that you are bought into your customer’s success, you care as much about their success as they do, they’ll keep you along for a long time.

Last question, coming back to the idea of success odds. If you had to give one piece of advice to someone about maximizing their long-term career upside, what would it be? Stacking the odds in their favor?

I think that one of the biggest things we can do right now is give ourselves some external indicators of credibility. I think that credibility is just becoming more and more important. Being a writer for the Harvard Business Review opens a lot of doors for me. Letting people go to the Penguin Random House website and see my book opens a lot of doors for me. We’re looking for ways to be different, and I think when we’re different in ways that feel credible, that’s really important.

Right now, we have more information than ever before. The differentiator is, is it credible information? Can I trust this information? Whatever you can do to go out and pursue those goals that put you in a position where people recognize, “This is somebody who has some authority in this space. This is somebody I can trust to help me distinguish the signal from the noise,” is going to be really powerful for you. Your skills are going to matter a lot, but what you’re looking for is these sources of credibility. I think those are the things that, even though they feel a little arbitrary, they set you apart in a world that often blends together.

To me, this whole idea of reducing the odds of failure, increasing the odds of success, it’s so intuitive, and yet people don’t really go through that mental exercise in any aspect of their life in terms of trying to stack the odds in their favor. That’s ultimately the key message you’re trying to convey to them.

Yeah, it’s uncomfortable to think about the things that could go wrong. We want to just imagine it going right. There is a skill that’s hidden within all this, that you have to learn how to be uncomfortable for a little bit. What I have found is when you identify the risks to your success, if you’re willing to sit in that discomfort for a little while, the solution almost always presents itself.

I was looking for just an example in the book. I knew I needed a case study for something. I was in an airport and I walked past a Ben & Jerry’s, and I thought, “I’ve been to Vermont, to the Ben & Jerry’s factory. I’ve seen the graveyard of all their failed flavors. I know that they had a really iterative process to succeed. I bet this is a story I can work with.”

I went back and sure enough, it worked great, made it into the book. It just comes with being willing to be uncomfortable for a little bit, trusting that you will figure this out. Not everything, but you’re going to put yourself in a position where you’re going to have ideas, you’re going to have options to choose from. You don’t have to be afraid of acknowledging that there are threats to your success.

You can trust that over time and through collaboration with other people, you’re going to be able to find some of those answers. A success diagram makes asking for advice a lot easier because you can share a context. “Here’s what I’m after, here’s what I think has to go right, here’s what I perceive that can go wrong, help me think this through.” that’s a lot better than just saying, “What would you do if you were me?”

Absolutely. Thank you, Kyle. It’s been a fun conversation, certainly a thought-provoking one, and I appreciate you making time for it.

I’ve enjoyed it. Thank you.

Alright, really interesting conversation. What are the practical takeaways from my discussion with Kyle just now? One, and I think most importantly, is this idea that success isn’t just about working harder, it’s about increasing your odds. That involves looking at both what it’s going to take to succeed and what could get in your way, the things that could cause you to fail.The people who are doing this best, they’re not necessarily the most talented people, but they’re designing their decisions and their actions and their environments to tilt probabilities in their favor over time. I think that’s the key message from Kyle’s book.

Second, and he talked about this in his own experience, setbacks can feel like detours but they also provide data. When you have a disruption, like the layoffs that Kyle went through, or failures that are in a business strategy, you can use them to recalibrate. To recalibrate your strategy, to think about your positioning, and to take smarter shots going forward.

Finally, differentiation, as we talked about at the end, is really an advantage. Whether you are thinking about this individually or you’re thinking about this from the perspective of a business, in a crowded market, blending in kills your odds.Standing out, sometimes even imperfectly, dramatically increases the chances of meaningful opportunities.

We see this with people who’ve overcome odds and doing things that nobody thought that they could do. Take some of those lessons to the way that you think about your own career journey. I invite you to subscribe to Career Sessions on Apple Podcasts and Spotify. You can also subscribe to our youtube channel, and if you found this discussion enlightening, sign up for my membership community, which is called Pathwise, and our newsletter Pathwisdom. Thanks, see you next time.

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About Kyle Austin Young

Kyle Austin Young is an award-winning strategy consultant for leaders and teams in a wide range of fields. At the core of his methodology is a powerful system for accomplishing big, meaningful goals that focuses on understanding and changing your odds of success. The nicest compliment Kyle has ever received happened unexpectedly when the phone rang during dinner.

The biotech CEO on the other end was brief. “I just felt like I should tell you that you’re the first consultant we’ve ever worked with who did exactly what he said he was gonna do.” That was nearly a decade ago, and it has set the tone for everything since.